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6928671 
Journal Article 
Synthesis of 1,3,5-Tris[(4 '-ethynylphenyl)ethynyl]benzene 
Chen Qiuyan; Ma Yuwen; Wang Chengyun; Shen Yongjia; , 
2012 
1 
Youji Huaxue / Chinese Journal of Organic Chemistry
ISSN: 0253-2786 
SCIENCE PRESS 
BEIJING 
1526-1532 
WOS:000308837200024 
Several synthetic routes were designed to prepare 1,3,5-tris[(4-ethynylphenyl)ethynyl]benzene. The synthetic routes and reaction conditions were contrasted and discussed, when multiple Sonogashira reactions were occurred between multifunctional alkyne-terminal compounds and aromatic bromine compounds, the different substitution degree compounds with similar polarity were obtained, and they were difficult to separate. Whereas the reactions between multifunctional alkyne-terminal compounds and aromatic iodine compounds can avoid this situation. 1,3,5-Tribromobenzene reacted with 3-methylbutynol to afford 1,3,5-tris(3'-hydroxy-3'-methyl-but-1'-ynyl)benzene, then 1,3,5-triethynylbenzene was obtained by the cleavage reaction of the compound in presence of potassium hydroxide and toluene. On the other hand, using 4-iodoaniline and trimethyl silyl acetylene as raw materials, 4-trimethylsiylethynyl iodobenzene was synthesized by diazo reaction and halogenation. Therefore, 1,3,5-tris[(4'-ethynylphenyl)ethynyl]benzene was prepared by the cleavage reaction of the 1,3,5-triethynylbenzene and 4-trimethylsiylethynyl iodobenzene. The structures of the target compound and intermediates were confirmed by H-1 NMR, C-13 NMR techniques and element analysis.